Wilmersdorf



Patented June 5, 1928.

UNITED STATES PATENT OFFICE.

WALTER SCHOELLER, OF BERLIN-WESTEND, AND HERBERT SCHOTTE, OF BERLIN- WILMERSDORF, GERMANY, ASSIGNORS TO THE FIRM CHEMISCHE FABBIK AU! ACTIEN (VORM. E. SCHLEBING), OF BERLIN, GERMANY.

CAMPHORIC ALKALOIDS AND PROCESS OF MAKING SAME.

No Drawing. Application filed March 18, 1927, Serial No. 175,923, and in Germany April 15, 1826.

Our invention refers to new products having valuable therapeutical properties and to the process of making same. It more particularly concerns alkaloid compounds of camphoric acid. Camphoric acid, slmllal to other bicarboxylic acids, is known to form two 'kinds of salts, neutral and acid salts. \Ve have now ascertained that, con trary to what could be expected, alkaloids which are capable of paralyzing the nervus vagus as for instance hyoscyamin, scopolamin, and atropin will combine with carnphoric acid in the molecular proportion of 1:1, even though added in excess of the molecular quantity. We have further found that it is immaterial whether the acid and the base are mixed in organic solvents such as ether, alcohol, and the like, or in watery solution in the form pf salts."

Obviously the possibility of producing in this manner homogeneous well crystallized salts involves a substantial simplification, for instance in the case where solutions with an unknown content of the alkaloid are em-" 2 loved. The new compounds obtained are istinguished by their extraordinary therapeutical effect on the nervus vagus. Example 1.2 grams camphoric acid an 3 grams hyoscyamin are dissolved separately in absolute ether and the solutions are then mixed, whereupon the camphoric salt will be precipitated at once in microcrystals having a melting point of about 168 C. v Example .2.-6.4 grams scopolami'n hydrate are dissolved in 100 grams ether and to the solution thus obtained is added a solu tion of 4 grams camphoric acid in 20 grams ether, The precipitated salt foru'is crystals having a melting point of about 145 C. 40 Example 8.T0 a neutral solution of atropin hydrochloride is added camphoric sodium and the mixture is evaporated. The

forms an alkaloid which exerts a paralyzing effect on the nervus vagus, such salt being a combination of 1 mol. of the cam horic acid radical and 1 mol. of the alkaloi and forming crystals, such product exerting a vigorous therapeutical effecton the nervus vagus.

2.. As anew product, camphorio scopolamin forming crystals melting at about 145C. and having a vigorous therapeutical effect on the nervus vagus.

3. The method of roducing salts of camphoric acid and alka ioids having a paralyzing effect on' the nervus vagus, comprisin acting with cam horic acid on a. solution 0 an alkaloid of t e kind described and cansing crystallization of the compound formed in the solution.

4. The method of producing camphoric scopolamin comprising acting with solution '75 of scopolamin on camphoric acid.

5. The method of producing scopolamin comprising acting with an etheric solution of 6,4 parts scopolamin hydrate on an etheric solution of 4 parts camphoric acid.

In testimony whereo we aflix our signa tures.

. WALTER SCILIOELLER. HERBERT SOHOTTE.

camphoric e 

